Between Sips
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.
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Is There Something Your Tax Return Isn't Telling You?
04/01/2026
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 Connect with us: Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: Listen to Off The Wall, our podcast with market analysis:
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Real Estate Ownership: Personal vs. LLC – What You Need to Know
03/18/2026
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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: Listen to Off The Wall, our podcast with market analysis:
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Retirement Accounts and The Tax Surprise Hiding in Your IRA
03/04/2026
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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: Listen to Off The Wall, our podcast with market analysis:
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Trump Accounts: What’s the Catch With the Free $1,000?
02/19/2026
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: LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: Instagram: Listen to Off The Wall, our podcast with market analysis:
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Do I Need a Trust? Here’s How They Work
02/04/2026
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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: Check out our Off The Wall podcast:
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The Conversation We All Keep Dodging: Estate Planning
01/21/2026
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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#
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How to Set Goals Without Overhauling Your Life in 2026
01/07/2026
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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: Instagram:
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What People Get Wrong About Roth IRAs and Conversions: A Guide for Busy Professionals
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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#
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How to Plan for Your Child’s Education
11/26/2025
How to Plan for Your Child’s Education
College can feel far away when your kids are still young, but the questions around their future tend to show up early. Over a favorite cup of coffee, Emily Harper, CFP® and Jessica Gibbs, CFP®, talk through the mix of hope, uncertainty, and planning that surrounds education today. They share what they’ve learned as financial planners and college graduates, touching on rising costs, changing career paths, and the value of defining your own philosophy before focusing on numbers. The conversation wanders through personal stories, shifts in the education landscape, and the small steps families can take now to create more options later. It’s an easygoing chat that leaves you feeling more grounded, more informed, and more prepared to shape opportunities for the kids you love. A sip worth settling into. Please see important podcast disclosure information at 0:00 – The Sips, and Why Education Planning Matters 3:00 – How Education Is Changing: AI, Jobs, and the Value Beyond Academics 9:00 – The Cost Conversation: Tuition Trends, Philosophy, Debt, and Aid 17:00 – Balancing College Priorities With Long-Term Goals 19:08 – 529 Plans: Flexibility, K-12 Uses, Trades, and Rollovers 28:00 – Funding Strategies: Superfunding, Consistency, and Alternatives 36:00 – Pulling It Together: Planning for Optionality Connect with us: Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: Instagram: https://www.instagram.com/monumentwealth/#
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Retiring Before 65: What It Really Means
11/12/2025
Retiring Before 65: What It Really Means
We’ve all heard 65 is the magic retirement age, but who decided that, anyway? In this episode, Jessica Gibbs, CFP®, and Emily Harper, CFP®, share a fresh take on what it means to step away from full-time work before that milestone. The conversation moves between money and mindset, the realities of healthcare and savings, and the freedom of redefining what retirement even looks like. They talk through how to prepare, what “enough” might mean for you, and why the emotional side of this transition matters just as much as the financial one. For anyone wondering when work starts to give way to something new, this sip is a thoughtful look at creating balance and space for the life you’ve been building toward. 0:00 – Disclaimers, coffee talk, and the Annapolis fall blend ☕️ 2:14 – Why some people dream of retiring before 65 and what that really means 4:45 – Where “65” came from, Social Security, and the real cost of healthcare before Medicare (COBRA tips included) 12:40 – How saving rates, wealth accumulation, and account mix shape your flexibility later on 22:10 – Building cash reserves, understanding spending habits, and preparing for down markets 28:12 – Earning in retirement, finding purpose, and keeping alignment with your spouse through the transition 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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#
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Should You Retire When the Market is Down?
10/29/2025
Should You Retire When the Market is Down?
Markets are down, your retirement date’s circled on the calendar—now what? Emily and Jessica unpack how to protect your peace of mind, why your “sleep-at-night factor” matters, and what it really means to retire on your terms. Tune in to hear how market volatility can impact your retirement portfolio if it happens at the wrong time. Plus, understand the value of stress-testing your portfolio and how to reduce your anxiety around retirement. Please see important podcast disclosure information at 0:14 - Intro 2:39 - Can You Retire in a Down Market? 5:18 - Why Timing of Returns Matters 14:40 - Beyond Markets: Inflation and Rates 17:05 - The Cash Bucket Strategy 20:05 - Key Takeaways 26:11 - Disclosures & Closing 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: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#
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OBBBA Review: Tax Moves to Make Before 2025 Ends
10/15/2025
OBBBA Review: Tax Moves to Make Before 2025 Ends
The “One Big Beautiful Bill” is here—and it’s changing the math on deductions, income timing, and year-end tax strategy. In this episode we cut through the complexity to spotlight the most important moves to make before December 31, 2025. We unpack what high earners need to know about charitable deductions, the new 35% cap, clean-energy credits, and how to make the most of your AGI and MAGI thresholds—without drowning in details. Pour yourself a cup of your favorite brew and tune in for clear, actionable ideas on how to finish the year tax-savvy and confident. Please see important podcast disclosure information at 0:00 – Why careful planning matters before 2025 0:19 – Important disclosure from Monument Wealth Management 2:10 – The “One Big Beautiful Bill Act” explained 4:09 – How the new tax code adds complexity 7:50 – Managing income thresholds and deductions 11:14 – Year-end moves to consider for 2025 15:00 – Energy credits and charitable giving changes 18:31 – The long-term view and the value of professional advice Connect with us: Get our Free Private Wealth Advice Newsletter: LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: Instagram:
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Unique Ways to Donate to Charity Beyond Writing a Check
10/01/2025
Unique Ways to Donate to Charity Beyond Writing a Check
“Cash isn’t the only way to make an impact. Complex assets—like private business shares or alternative investments—can sometimes be the most powerful gifts.” Emily M. Harper, CFP® Charitable donations come in many forms: cash, stock, assets. In this episode, we’re talking about charitable donations in the form of complex assets, such as privately held business shares, crypto, oil and gas royalties, and more. Depending on your situation, it may make a lot of sense. It can help maximize the impact of your gift while also increasing your tax efficiency. That being said, there is much to consider, so we’re breaking it all down for you. Join us as we discuss when donating complex assets makes sense, how to do it, and what to expect when you go through the process. Please see important podcast disclosure information at 0:58 – Donating complex assets 3:23 – Tax benefits of appreciated assets 6:30 – Donor-advised funds option 9:28 – Charity due diligence 12:24 – Third-party appraisals 16:25 – Time and complexity 19:52 – Charitable intent first Resources Mentioned: Off The Wall Episode 66: From DAFs to Charitable Trusts: Choosing the Right Path for Meaningful Philanthropy. Connect with us: Get our Free Private Wealth Advice Newsletter: LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: Instagram: /#
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Post-Exit Planning: How to Manage Your Investments & Cash Flow After Selling Your Business
09/17/2025
Post-Exit Planning: How to Manage Your Investments & Cash Flow After Selling Your Business
For business owners, the day you sell your business can feel like you’re crossing the finish line. In reality, it’s actually just a new starting point for the beginning of your post-exit life. One of the biggest questions we hear after a successful sale is “What should I do with all this money?” In this episode, Jessica and Emily tackle the financial side of post-exit life: the benefits of a cash strategy, why you should be thinking about your portfolio’s total return (not just income), and why behavior is often the biggest threat to long-term investing success. Tune in to learn more about how you can build an option-rich life after selling your business. Please see important podcast disclosure information at Connect with us: Get our Free Private Wealth Advice Newsletter: LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: Instagram:
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Life After Ownership: Defining Your Next Chapter After You Sell a Business
09/03/2025
Life After Ownership: Defining Your Next Chapter After You Sell a Business
“Liquidity can open a lot of doors, but purpose tells you which ones to walk through.” Selling a business is an amazing accomplishment, but it is often followed by an identity crisis that can leave former business owners in a spiral. The purpose you committed yourself to every day is suddenly gone – what’s your purpose now? In this episode, we discuss how to approach life after business-ownership: how to find fulfillment, what to do with the money, and where to look for your next project.Whether that’s joining a board, angel investing, or pursuing philanthropic endeavors–Jessica and Emily share ideas and scenarios to consider. Join us for a great conversation and great coffee! Please see important podcast disclosure information at Connect with us! Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe LinkedIn: Connect with Emily on LinkedIn: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: https://www.instagram.com/monumentwealth/#
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A Gift that Changes the Game: How to Approach Transformational Giving
08/20/2025
A Gift that Changes the Game: How to Approach Transformational Giving
What if your giving could transform an organization’s future? In this episode of Between Sips, we share how to approach extraordinary charitable gifts—whether $25K or $25M—with intention and impact. We’ll cover the four factors to consider, smart questions to ask the charity, and how to navigate recognition, structuring your gift, and assessing impact. Tune in to learn how to turn generosity into truly strategic giving. Please see important podcast disclosure information at Connect with Monument Wealth Management:
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Thinking of Moving or Retiring Abroad? Listen to This Episode First
08/06/2025
Thinking of Moving or Retiring Abroad? Listen to This Episode First
Welcome to the inaugural episode of “Between Sips,” a new podcast from Monument Wealth Management where we look at big questions at the intersection of money and meaning. In this episode, we’re answering the question: Should I move–or invest–abroad? We talk about what to expect, what’s involved, and how to prepare. When people dream of retiring abroad, they typically think of margaritas on the beach and sipping wine in the Riviera, not the intricacies of international tax laws. From visas to tax issues to cost of living and more, moving to a foreign country comes with a lot of baggage, both literal and metaphorical. Listen in to find out how you can start planning your dream life abroad – without leaving out the reality! Please see important podcast disclosure information at Connect with us: /emilyharpercfp /jessicagibbscfp
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