Managing To Be Wealthy

Managing To Be Wealthy

By John E. Sestina and CompanyBusinessInvestingBusiness News
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Managing To Be Wealthy episodes

  • 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 […]
    21 min
  • 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 […]
    29 min
  • 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 […]
    23 min
  • 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 […]
    30 min
  • 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 […]
    22 min
  • 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 […]
    32 min
  • 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). […]
    27 min
  • 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 […]
    23 min
  • 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 […]
    25 min

About Managing To Be Wealthy

From the publisher's feed

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?”—offering valuable takeaways for listeners at every stage of life. You can tune in anytime, wherever you stream your podcasts. If you have a question or would like to join the conversation, we’d love to hear from you.