Between Sips

Monument Wealth Management
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Pull up a chair, pour your favorite drink, and join Monument Wealth Management partners Jessica Gibbs, CFP®️ and Emily Harper, CFP®️ for candid, coffee-table conversations about money, meaning, and the moments that matter. We're answering the most pressing questions successful people have about creating and preserving their wealth, along with and a human take on making life option rich—served one sip at a time. Have a wealth management question you want answered? Send it to us at betweensips@monumentwm.com.

  1. 1D AGO

    Is There Something Your Tax Return Isn't Telling You?

    You've got a good accountant. You trust them. You sign the return. But here's what Emily and Jessica see all the time: costly mistakes that aren't anyone's fault — they happen because your accountant can only work with what they're given. And there are things living at the intersection of your tax return and your busy life that fall through the cracks unless someone is paying attention to the whole picture. In this episode, Emily and Jessica walk through what your tax return is actually telling you — and what it should be driving. Because the number at the bottom isn't the point. The point is what that document reveals about the decisions in front of you right now: whether to do a Roth conversion this year, how to think about RSU timing, whether your charitable giving strategy is actually working as hard as it could, and why the income decisions you make today will show up in your Medicare premiums two years from now. They also cover the mistakes that are easy to miss and expensive to fix — including one that causes people to pay income tax on money they already gave to charity. If your tax return has been a once-a-year checkbox, this episode will change how you think about it. ☕ Today's sip: Buffalo Blend from Airship Coffee, a roaster in Bentonville, Arkansas.   0:00 — The Social Security Mistake Nobody Talks About  0:52 — Why Your Tax Return Is More Than a Number  2:18 — What We're Sippin' on Today  2:45 — How to Review Without the Overwhelm  6:54 — Income Schedules Worth a Second Look  11:15 — Deductions You Could Be Leaving on the Table  17:38 — Estimated Tax Payments: What You Have to Track Yourself  18:52 — How Your Tax Return Should Be Driving Financial Decisions  27:10 — Where to Find Us   Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures Connect with us:    Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

    30 min

  2. MAR 18

    Real Estate Ownership: Personal vs. LLC – What You Need to Know

    If you've spent any time on financial social media, you've probably heard some version of this: buy real estate, put it in an LLC, and watch the tax savings roll in. Here's the thing — that's mostly wrong. And in this episode, Emily and Jessica explain why. For most high earners, rental real estate is a passive activity. The deductions don't touch your W-2 income. The LLC doesn't change what hits your tax return. And qualifying for the tax treatment people are actually imagining? That requires a level of real estate involvement that most busy professionals simply don't have. So if it's not really a tax decision — what is it? That's where the conversation gets interesting. Emily and Jessica get into the real reasons entity structure matters: liability exposure, estate planning, and what happens to that beloved family beach house when you're gone. Less clickbait, more clarity. That's this episode.   0:56 — The Core Question and Short Answer 1:48 — What We're Sippin' on Today 2:11 — Why Real Estate Tax Hacks Spread 3:13 — Passive Loss Limits and Depreciation 5:20 — Why an LLC Is Not Magic 7:21 — Audit Risk and Schedule E Basics 10:15 — The Bigger Issue Is Liability 13:41 — Estate Planning and Shared Family Homes 16:45 — Get Real Advice, Not Social Media Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:    Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

    20 min

  3. MAR 4

    Retirement Accounts and The Tax Surprise Hiding in Your IRA

    There's this belief a lot of smart, responsible people carry for decades: Save as much as possible in your retirement accounts, don't touch it, let it grow, future you will thank you. And then…future you hits "RMD age". Suddenly there's a number attached to your birthday. A required withdrawal. A tax bill you didn't fully picture. Medicare premiums reacting to your income. And the realization that most of your wealth lives in accounts the IRS still has a claim on. This conversation with Jessica and Emily feels like the moment when you zoom out and look at your entire financial life instead of just one account. It's about control. About flexibility. About asking better questions before the rules start making decisions for you. Because retirement should be about using it while you have the energy, the health, and the curiosity to enjoy it. And sometimes the smartest move isn't waiting, but planning earlier, so you don't feel boxed in later. Coffee in hand. Big-picture thinking activated.   0:00 — The Big RMD Question 2:21 — Why Waiting Can Backfire 4:30 — The New Retiree Balance Problem 6:20 — How RMDs Push You Up Tax Brackets 9:05 — Real Numbers + Medicare Ripple Effects 12:05 — Smart Moves Before RMD Age 15:10 — Inheritance, Psychology, and Spending Flexibility Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:    Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

    22 min

  4. FEB 19

    Trump Accounts: What's the Catch With the Free $1,000?

    With headlines, commercials, and social chatter everywhere, these new accounts are getting a lot of attention. But are they actually the best way to give kids a financial head start? In this episode of Between Sips, Emily and Jessica break down how Trump accounts work, where they fit alongside 529s and custodial accounts, and why your child's future goals should drive every decision. They share what high-earning families need to know about tax treatment, flexibility, record-keeping, and the trade-offs that often get overlooked. If you're saving for a new baby—or just trying to make smarter decisions for the next generation—this conversation will help you focus on what actually moves the needle. Grab your coffee and listen in.   0:00 — Big Question: Should You Open a Trump Account? 3:16 — Why They're Trending (And What the Hype Misses) 6:04 — How Trump Accounts Actually Work 10:02 — Withdrawal Rules, Penalties & Fine Print 12:15 — Growth Projections vs. Reality 16:53 — 529s and Custodial Accounts Compared 20:30 — Practical Takeaways for Parents Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:  Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe   LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/  Instagram: https://www.instagram.com/monumentwealth/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

    24 min

  5. FEB 4

    Do I Need a Trust? Here's How They Work

    Trusts aren't just for the ultra wealthy, or something you deal with much later in life. For most people, that assumption just creates stress and delay. In this episode of Between Sips, Emily and Jessica slow things down and talk about trusts in plain language. What they are, why people use them, and why they are not magic tax loopholes. You'll hear the difference between revocable and irrevocable trusts, explained with everyday examples. This conversation will help you feel less intimidated and more grounded. You don't have to rush out and set something up tomorrow, but you should understand what questions are worth asking when the time comes.   0:00 — Disclosures, Coffee, And Why Trusts Feel Intimidating 4:07 — Revocable Trusts Explained With A Ziploc Bag 9:15 — Irrevocable Trusts And What You Give Up 17:40 — Probate, Privacy, And Common Tax Myths 24:09 — Choosing Trustees And When Corporate Help Matters 32:07 — Fairness, Incentives, And Making A Plan That Works Now   Resources Mentioned: How to know if it's time for a corporate trust: https://monumentwealthmanagement.com/resource/how-to-know-its-time-for-a-corporate-trustee/ Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:    Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/# Check out our Off The Wall podcast: https://monumentwealthmanagement.com/off-the-wall-podcast/

    38 min

  6. JAN 21

    The Conversation We All Keep Dodging: Estate Planning

    Estate planning has a reputation for being heavy, uncomfortable, and easy to avoid. Between sips of a Rhode Island coffee, Jessica and Emily talk about why that avoidance is so common, even among thoughtful and successful people, and why it can create more stress down the road. This conversation reframes estate planning as a way to protect your life, your relationships, and the people you love, not a checklist for the end of life. From incapacity planning to outdated documents, they explore how small decisions today can create clarity and peace of mind later, without making it overwhelming.   0:00 — What We're Sippin' on Today 2:12 — Whole-Life Lens On Estate Planning 4:50 — Why Successful People Delay 12:55 — Incapacity And Clarity In Crisis 17:19 — Guardianship And Wills For Parents 22:11 — Outdated Docs And Beneficiary Traps 26:18 — Will vs Trust And Funding A Trust 31:20 — Powers Of Attorney And Directives 36:05 — Getting Started And Practical Next Steps 39:31 — Reviews, Audits, And Advisor Support —- Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:  Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#

    40 min

  7. JAN 7

    How to Set Goals Without Overhauling Your Life in 2026

    A new year has a way of making people feel like they need to figure everything out at once. Goals, priorities, plans, all piled together in January, like our life restarts with the change in the calendar. In this first Between Sips episode of 2026, Emily and Jessica talk through a more realistic way of thinking about goals, one that leaves room for life stage, time constraints, and changing priorities. They share why so many people struggle to articulate what they want, and how narrowing goals too quickly can cause us to miss opportunities that really move the needle. The conversation takes into account experiences, health, career, relationships, creativity, and giving, not as a checklist, but as different parts of life that often compete for attention. Along the way, we reflect on how money fits into all of it, not as the point of the plan, but as something that supports the choices successful people make. This episode is for anyone heading into 2026 feeling thoughtful rather than decisive, and looking for a steadier way to think about the year ahead.   0:00 — Champagne, A New Year, And Fresh Starts 4:40 — Why Goals Need Meaning 9:40 — The Bucket List Framework And Three Goal Buckets 15:20 — Health, Stress, And Spending Without Guilt 23:00 — Career Growth, Creativity, And Cash Flow Confidence 32:10 — Relationships, Time Poverty, And Support 39:20 — Finance As An Enabler, Not The Goal Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:  Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#

    40 min

  8. 12/10/2025

    What People Get Wrong About Roth IRAs and Conversions: A Guide for Busy Professionals

    Roth IRAs, backdoor Roths, conversions… most people know these terms, but not why they matter. In this episode, Emily and Jessica break it all down in plain English and focus on the real question: How do you create more flexibility for your future self? With uncertainty around tax policy and retirement rules, the way your money gets taxed can have as much impact as how it's invested. The good news? You have more control than you may think. Emily and Jessica walk through the key moments when a Roth conversion might be worth considering—career pivots, sabbaticals, business transitions, lower-income years—and how building a mix of account types can give you more options in retirement and beyond. If you want to understand why Roths matter (not just how they work), this episode is for you. 👉 Grab your cup o' tea (or joe) and listen in Between Sips.   0:00 – What We're Sipping On 2:05 – Why Roth Conversions Matter 4:45 – When Conversions Make Sense During Working Years 8:15 – Roth 401k Options, Backdoor Paths, And Income Limits 15:20 – How Roth Conversions Work And Key Tax Considerations 18:00 – RMD Relief, Inheritance Benefits, And Planning Risks   Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures Connect with us:  Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe  LinkedIn: https://www.linkedin.com/company/monument-wealth-management/  Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/ Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#

    35 min
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5
out of 5
7 Ratings

About

Pull up a chair, pour your favorite drink, and join Monument Wealth Management partners Jessica Gibbs, CFP®️ and Emily Harper, CFP®️ for candid, coffee-table conversations about money, meaning, and the moments that matter. We're answering the most pressing questions successful people have about creating and preserving their wealth, along with and a human take on making life option rich—served one sip at a time. Have a wealth management question you want answered? Send it to us at betweensips@monumentwm.com.

Information

  • Creator
    Monument Wealth Management
  • Years Active
    2025 - 2026
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © Monument Capital Management
  • Show Website
    Between Sips