PODCAST · business
Managing To Be Wealthy
by John E. Sestina and Company
Managing to Be Wealthy® is one of the nation’s premier financial planning podcasts—informative, innovative, and rooted in real-world experience. Hosted by Tracey Bennett and our team of CERTIFIED FINANCIAL PLANNER™ professionals, each episode blends decades of insight with relatable conversations to help you take charge of your financial life with clarity and confidence. Produced by John E. Sestina and Company in tandem with Boxland Media, LLC, a fee-only financial planning firm registered with the SEC and based in Columbus, Ohio, the podcast reflects a philosophy more than 50 years in the making. Grounded in our comprehensive and time-tested approach, Managing to Be Wealthy®, we deliver planning guidance that is personal, practical, and built around your goals—because peace of mind is the true measure of wealth. Each weekly episode covers timely and timeless topics alike—from “Do you feel financially secure for retirement?” to “What does it take to become financially independent?”—off
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147
Episode 371: Protecting Parents: Financial Moves for Parents in Declining Health
When a parent’s health changes fast, families are forced into financial decisions they never expected to make. In this episode, we walk through the real‑life choices adult children face—from care decisions and using the family home to coordinating siblings and protecting their own financial future—when everything feels uncertain and rushed.When a parent’s health changes fast, […]
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146
Episode 370: Retiring Before 65: How to Cover Yourself Until Medicare Kicks In
Retiring before 65 means planning for the years before Medicare begins. This episode highlights practical ways to stay insured during that gap—COBRA, ACA plans, employer retiree options, part‑time work with benefits, and other temporary coverage paths—so you can move into early retirement with fewer surprises around healthcare costs.Retiring before 65 means planning for the years […]
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145
Episode 369: Layering Life Insurance Policies for Different Life Stages
We’re turning life insurance into adulting Jenga: stack short-, mid-, and long-term term policies so you’re not paying 30-year prices to cover a 5-year problem. Permanent insurance makes a classy cameo (estate plans, business stuff), while cash‑flow math body‑checks the hard sell. We’ll prep you for health plot twists, share Plan B if underwriting swipes […]
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144
Episode 368: Sharing A Home Without Marriage
Sharing a home with someone—no matter the relationship—comes with real money choices and no built‑in rulebook. This episode breaks down the conversations that keep co‑living fair, clear, and financially steady when you’re building a life under one roof in your own way. Sharing a home with someone—no matter the relationship—comes with real money choices and […]
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143
Episode 367: Taxes and Beyond- The Foundation of Your Wealth Strategy
Unlock more of what you keep by making tax work for you—not against you. We cover simple ways to free up cash flow today, turn debt and major purchases into tax‑smart moves, gift strategically, protect your estate, and coordinate investments and retirement benefits—so your wealth plan goes beyond April 15. Important Note: The content shared […]
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142
Episode 366: Grasping How Our Minds Affect Investing – Throughout Market Ups and Downs
Sometimes it’s your brain vs. The Market – and can be a relatable matchup Investing isn’t just numbers—it’s nerves, instincts, headlines, and that little voice in your head that panics at the exact wrong moment. In this episode, we explore how our minds shape the way we react to market swings, why emotions love to […]
-
141
Episode 365: IOUs and Family Ties – Lending Without the Stress or the Mess
What if helping family could feel good, stay simple, and strengthen your relationships along the way? This episode explores how to support the people you love without stress, confusion, or awkward money moments — just clear intentions, healthy boundaries, and confidence in the choices you make. Important Note: The content shared is for informational purposes […]
-
140
Episode 364: Navigating Financial Growth in Subscription-Driven Businesses
Running a subscription business feels amazing—money shows up on schedule like a well‑trained golden retriever. Expenses, however, behave more like a raccoon in your trash cans. In this episode, we break down how to budget during those “good months,” save for taxes before they sneak‑attack you, and reinvest without buying every shiny tool the internet […]
-
139
Episode 363: Roth conversion strategies across life stages
Tax Now, Party Later. A Roth conversion is basically choosing to pay taxes now so Future You can live their best tax‑free life. In this episode, we show how it plays out in your 20s and 30s (cheap taxes!), your 40s and 50s (timing is everything), and retirement (the golden “convert before RMDs attack” window). […]
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138
Episode 362: Estate Plans Without Family Governance: Like a Car Without a Driver
Picture a legacy that practically runs itself—not just because the paperwork is solid, but because everyone already knows how to carry the plan forward with confidence. This episode explores the behind‑the‑scenes structure that helps families stay coordinated, informed, and genuinely connected as they move through the future together. Important Note: The content shared is for […]
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137
Episode 361: The Sequence of Savings Funding HSA, Roth, 401(k), or Taxable First
What if saving wasn’t about rules at all — but about unlocking the smartest sequence for building real financial freedom? This episode peeks behind the curtain at how savvy savers quietly turn everyday choices into long‑term power moves… and why where you stash your next dollar might matter more than how much you save. Think […]
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136
Episode 360: Equity Compensation Unlocked – Turning Stock into Strategy
Ever wondered how to turn company stock into real strategy? This episode breaks down RSUs, stock options, ESPPs, tax timing, concentration risk, and what to do when big liquidity events hit. We’ll talk through how equity can fund real‑life goals, how to avoid surprise taxes, and how to build a plan that grows with you—simple, […]
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135
Episode 359: Beyond the Nest- Power Moves for Your Next Wealth Chapter
As you approach your next wealth chapter, this conversation digs into how to redirect extra cash more intentionally, sharpen your tax and investing moves, refresh estate and insurance plans, and prep confidently for big financial decisions—all while keeping an eye on long‑term goals, family conversations, and the mindset shifts that come with major life transitions. […]
-
134
Episode 358: Boomer Futures – Planning to Live Long, Live Well, and Leave on Your Terms
Boomers aren’t just aging — they’re redefining what the next 30 years can look like. This episode dives into how today’s longest‑living, most financially powerful generation can turn longevity into leverage. We’re talking thriving into your 90s, supporting kids and parents without losing momentum, navigating rising health costs with confidence, building a retirement paycheck that […]
-
133
Episode 357: Peace of Mind in Your Lifetime: Planning for Loved Ones with Special Needs
When someone you love needs lifelong support, the decisions you make today can shape their security for decades. This episode pulls back the curtain on the thoughtful, behind‑the‑scenes choices families consider when building a plan that protects benefits, honors trust, and keeps everyone confidently aligned for the long run. Important Note: The content shared is […]
-
132
Episode 356: Gray Divorce: Protecting Wealth and Independence After 50
Splitting up after 50? Let’s make sure the only thing that breaks is the relationship, not your retirement plan. We’ll cover the big stuff: using QDROs without triggering tax nightmares, smart IRA moves, Social Security secrets (hello, 10‑year rule), and why “keeping the house” might actually be keeping you broke. We’ll also hit the must‑dos: […]
-
131
Episode 355: Smart Spending How Small Businesses Can Use Section 179 to Strengthen Their Financial Plan
Section 179 can be a real boost—if you use it with purpose. In this episode, we’ll talk about making confident, well‑timed decisions, choosing upgrades that actually move your business forward, and weaving tax strategy into a bigger financial plan – with the right pros in your corner. Important Note: The content shared is for informational […]
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130
Episode 354: Life After Graduation- Preparing Your College Grad for What’s Next
Post‑college life comes with paychecks, bills, decisions, and plenty of “wait… how do I do this?” moments. This episode helps new grads ease into adulthood with a simple, supportive look at money, work, and building confidence in the real world—served with a little humor to make the transition feel a lot less intimidating. Important Note: […]
-
129
Episode 353: Spending Smart in Retirement
You did the saving… so why does spending feel so uncomfortable? This episode walks through retirement income and withdrawals in a practical way that helps replace worry with confidence. Important Note: The content shared is for informational purposes only and should not be considered personalized financial, legal, or tax advice. We do not recommend specific […]
-
128
Episode 352: Boomers on the Move – Travel Trends & Financial Tips for the Golden Years
Travel is a top priority for many retirees—but how do you make it fit your financial plan? In this episode, we explore smart budgeting for bucket-list trips, maximizing travel rewards, planning for healthcare abroad, and avoiding scams. Plus, we cover estate considerations for foreign property and tips for balancing family travel with long-term financial health—so […]
-
127
Episode 351: Beyond the Mortgage Hidden Costs, Builder Buydowns & Protecting Your Home and Identity
Owning a home is more than a mortgage payment—it’s a whole ecosystem of costs, decisions, and “wait… no one told me that” moments. In this episode, we explore the often‑overlooked parts of homeownership, from surprising expenses to smart ways to protect both your property and your identity. With practical guidance, a little levity, and a […]
-
126
Episode 350: Demystifying the 403(b) What You Need to Know About Your Retirement Plan
A 403(b) can feel like one of those benefits you know is important—but aren’t totally sure how it actually works. In this episode, we break down what makes this plan unique, how to make the most of what your employer offers, and what to keep in mind as you build a retirement strategy that actually […]
-
125
Episode 349: Smart Debt Strategy: Using a HELOC to Accelerate Payoff
Thinking about using a HELOC to help tackle debt—but not sure if it’s a smart move or a risky one? In this episode, we walk through how a home equity line of credit works, why some people use it to pay down higher‑interest debt, and the trade‑offs to think about along the way. It’s a […]
-
124
Episode 348: Cash Flow Modeling for Early Retirement
Planning to retire early and wondering how the numbers actually shake out? In this episode, we break down cash‑flow modeling in a simple, conversational way—looking at how your timeline, inflation, healthcare costs, Social Security, and shifting spending habits all play into a long‑term plan. It’s a down‑to‑earth chat about building flexibility into your future and […]
-
123
Episode 367: Taxes and Beyond- The Foundation of Your Wealth Strategy
Unlock more of what you keep by making tax work for you—not against you. We cover simple ways to free up cash flow today, turn debt and major purchases into tax‑smart moves, gift strategically, protect your estate, and coordinate investments and retirement benefits—so your wealth plan goes beyond April 15. Important Note: The content shared […]
-
122
Episode 368: Sharing A Home Without Marriage
Sharing a home with someone—no matter the relationship—comes with real money choices and no built‑in rulebook. This episode breaks down the conversations that keep co‑living fair, clear, and financially steady when you’re building a life under one roof in your own way. Important Note: The content shared is for informational purposes only and should not […]
-
121
Episode 366: Grasping How Our Minds Affect Investing – Throughout Market Ups and Downs
Sometimes it’s your brain vs. The Market – and can be a relatable matchup Investing isn’t just numbers—it’s nerves, instincts, headlines, and that little voice in your head that panics at the exact wrong moment. In this episode, we explore how our minds shape the way we react to market swings, why emotions love to […]
-
120
Episode 365: IOUs and Family Ties – Lending Without the Stress or the Mess
What if helping family could feel good, stay simple, and strengthen your relationships along the way? This episode explores how to support the people you love without stress, confusion, or awkward money moments — just clear intentions, healthy boundaries, and confidence in the choices you make. Important Note: The content shared is for informational purposes […]
-
119
Episode 364: Navigating Financial Growth in Subscription-Driven Businesses
Running a subscription business feels amazing—money shows up on schedule like a well‑trained golden retriever. Expenses, however, behave more like a raccoon in your trash cans. In this episode, we break down how to budget during those “good months,” save for taxes before they sneak‑attack you, and reinvest without buying every shiny tool the internet […]
-
118
Episode 363: Roth conversion strategies across life stages
Tax Now, Party Later. A Roth conversion is basically choosing to pay taxes now so Future You can live their best tax‑free life. In this episode, we show how it plays out in your 20s and 30s (cheap taxes!), your 40s and 50s (timing is everything), and retirement (the golden “convert before RMDs attack” window). […]
-
117
Episode 362: Estate Plans Without Family Governance: Like a Car Without a Driver
Picture a legacy that practically runs itself—not just because the paperwork is solid, but because everyone already knows how to carry the plan forward with confidence. This episode explores the behind‑the‑scenes structure that helps families stay coordinated, informed, and genuinely connected as they move through the future together. Important Note: The content shared is for […]
-
116
Episode 361: The Sequence of Savings Funding HSA, Roth, 401(k), or Taxable First
What if saving wasn’t about rules at all — but about unlocking the smartest sequence for building real financial freedom? This episode peeks behind the curtain at how savvy savers quietly turn everyday choices into long‑term power moves… and why where you stash your next dollar might matter more than how much you save. Think […]
-
115
Episode 360: Equity Compensation Unlocked – Turning Stock into Strategy
Ever wondered how to turn company stock into real strategy? This episode breaks down RSUs, stock options, ESPPs, tax timing, concentration risk, and what to do when big liquidity events hit. We’ll talk through how equity can fund real‑life goals, how to avoid surprise taxes, and how to build a plan that grows with you—simple, […]
-
114
Episode 359: Beyond the Nest- Power Moves for Your Next Wealth Chapter
As you approach your next wealth chapter, this conversation digs into how to redirect extra cash more intentionally, sharpen your tax and investing moves, refresh estate and insurance plans, and prep confidently for big financial decisions—all while keeping an eye on long‑term goals, family conversations, and the mindset shifts that come with major life transitions. […]
-
113
Episode 358: Boomer Futures – Planning to Live Long, Live Well, and Leave on Your Terms
Boomers aren’t just aging — they’re redefining what the next 30 years can look like. This episode dives into how today’s longest‑living, most financially powerful generation can turn longevity into leverage. We’re talking thriving into your 90s, supporting kids and parents without losing momentum, navigating rising health costs with confidence, building a retirement paycheck that […]
-
112
Episode 357: Peace of Mind in Your Lifetime: Planning for Loved Ones with Special Needs
When someone you love needs lifelong support, the decisions you make today can shape their security for decades. This episode pulls back the curtain on the thoughtful, behind‑the‑scenes choices families consider when building a plan that protects benefits, honors trust, and keeps everyone confidently aligned for the long run. Important Note: The content shared is […]
-
111
Episode 354: Life After Graduation- Preparing Your College Grad for What’s Next
Post‑college life comes with paychecks, bills, decisions, and plenty of “wait… how do I do this?” moments. This episode helps new grads ease into adulthood with a simple, supportive look at money, work, and building confidence in the real world—served with a little humor to make the transition feel a lot less intimidating. Important Note: […]
-
110
Episode 356: Gray Divorce: Protecting Wealth and Independence After 50
Splitting up after 50? Let’s make sure the only thing that breaks is the relationship, not your retirement plan. We’ll cover the big stuff: using QDROs without triggering tax nightmares, smart IRA moves, Social Security secrets (hello, 10‑year rule), and why “keeping the house” might actually be keeping you broke. We’ll also hit the must‑dos: […]
-
109
Episode 355: Smart Spending How Small Businesses Can Use Section 179 to Strengthen Their Financial Plan
Section 179 can be a real boost—if you use it with purpose. In this episode, we’ll talk about making confident, well‑timed decisions, choosing upgrades that actually move your business forward, and weaving tax strategy into a bigger financial plan – with the right pros in your corner. Important Note: The content shared is for informational […]
-
108
Episode 351: Beyond the Mortgage Hidden Costs, Builder Buydowns & Protecting Your Home and Identity
Owning a home is more than a mortgage payment—it’s a whole ecosystem of costs, decisions, and “wait… no one told me that” moments. In this episode, we explore the often‑overlooked parts of homeownership, from surprising expenses to smart ways to protect both your property and your identity. With practical guidance, a little levity, and a […]
-
107
Episode 353: Spending Smart in Retirement
You did the saving… so why does spending feel so uncomfortable? This episode walks through retirement income and withdrawals in a practical way that helps replace worry with confidence. Important Note: The content shared is for informational purposes only and should not be considered personalized financial, legal, or tax advice. We do not recommend specific […]
-
106
Episode 352: Boomers on the Move- Travel Trends & Financial Tips for the Golden Years
Travel is a top priority for many retirees—but how do you make it fit your financial plan? In this episode, we explore smart budgeting for bucket-list trips, maximizing travel rewards, planning for healthcare abroad, and avoiding scams. Plus, we cover estate considerations for foreign property and tips for balancing family travel with long-term financial health—so […]
-
105
Episode 349: Smart Debt Strategy: Using a HELOC to Accelerate Payoff
Thinking about using a HELOC to help tackle debt—but not sure if it’s a smart move or a risky one? In this episode, we walk through how a home equity line of credit works, why some people use it to pay down higher‑interest debt, and the trade‑offs to think about along the way. It’s a […]
-
104
Episode 348: Cash Flow Modeling for Early Retirement
Planning to retire early and wondering how the numbers actually shake out? In this episode, we break down cash‑flow modeling in a simple, conversational way—looking at how your timeline, inflation, healthcare costs, Social Security, and shifting spending habits all play into a long‑term plan. It’s a down‑to‑earth chat about building flexibility into your future and […]
-
103
Episode 350: Demystifying the 403(b) What You Need to Know About Your Retirement Plan
A 403(b) can feel like one of those benefits you know is important—but aren’t totally sure how it actually works. In this episode, we break down what makes this plan unique, how to make the most of what your employer offers, and what to keep in mind as you build a retirement strategy that actually […]
-
102
Episode 347: 529 Plans and Scholarships- Smart Moves When Your Child Gets a Big Win
What happens when your child lands a big scholarship—and you still have money in their 529? In this episode, we break down the common “now what?” questions families face. We talk about using leftover funds without penalties, timing withdrawals, shifting beneficiaries, how scholarships interact with education tax credits, and whether extra 529 money could affect siblings’ […]
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101
Episode 345: Behavioral Triggers in Financial Decision-Making
Why do emotions drive money choices? We’re unpacking common biases—like loss aversion, anchoring, and herd mentality—and how they shape decisions every day. Tune in for practical insights on staying grounded and making smarter financial moves. Important Note: The content shared is for informational purposes only and should not be considered personalized financial, legal, or tax […]
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100
Episode 346: Charitable Giving via Donor-Advised Funds and Qualified Charitable Distributions
Want to give to charity and keep more in your pocket? We break down two powerful strategies—Donor‑Advised Funds and Qualified Charitable Distributions—so you can see how they work, who they help, and how timing your gifts can make a big difference. Educational only; not tax, legal, or investment advice. Important Note: The content shared is […]
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99
Episode 344: Open Enrollment Made Simple – Maximizing Your Benefits
Open enrollment doesn’t have to be overwhelming. In this episode, we break down the basics, compare health plans, and explain FSAs vs. HSAs, and show you how to maximize employer perks and retirement contributions. Practical tips, real-life examples, and strategies to avoid costly mistakes—so you can make confident benefit choices. Important Note: The content shared […]
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98
Episode 343: Year-End Financial Checklist: Setting Yourself Up for Success
Close out the year with confidence! This episode walks through smart moves to review your budget, maximize retirement contributions, fine-tune tax strategies, update insurance, and set exciting goals for the year ahead. Practical tips to help you start strong and stay on track. Important Note: The content shared is for informational purposes only and should […]
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ABOUT THIS SHOW
Managing to Be Wealthy® is one of the nation’s premier financial planning podcasts—informative, innovative, and rooted in real-world experience. Hosted by Tracey Bennett and our team of CERTIFIED FINANCIAL PLANNER™ professionals, each episode blends decades of insight with relatable conversations to help you take charge of your financial life with clarity and confidence. Produced by John E. Sestina and Company in tandem with Boxland Media, LLC, a fee-only financial planning firm registered with the SEC and based in Columbus, Ohio, the podcast reflects a philosophy more than 50 years in the making. Grounded in our comprehensive and time-tested approach, Managing to Be Wealthy®, we deliver planning guidance that is personal, practical, and built around your goals—because peace of mind is the true measure of wealth. Each weekly episode covers timely and timeless topics alike—from “Do you feel financially secure for retirement?” to “What does it take to become financially independent?”—off
HOSTED BY
John E. Sestina and Company
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