Between Sips

Monument Wealth Management
  • 5.0 (7)
  • INVESTING
  • UPDATED BIWEEKLY

Time for a coffee break? Jessica Gibbs, CFP®️ and Emily Harper, CFP®️ answer the most pressing questions successful people ask about using their wealth to create an option-rich life—served one sip at a time. Have a question you want answered? Send it to: betweensips@monumentwm.com

  1. 2D AGO

    Marriage + Money: What Women Need to Know

    Nearly 40% of women in heterosexual marriages now bring home the larger paycheck — yet a surprising number still hand off the financial decision-making to their spouse. Not because they lack the knowledge or confidence, but because life gets busy and the path of least resistance takes over. In this episode, Emily and Jessica dig into the "breadwinner mindset" — and why so many women don't claim it even when the numbers say they should. They explore what it really means to have your own financial identity inside a marriage: not as a backup plan or hedge against divorce, but as the foundation of a genuinely equal partnership. The conversation covers the practical side of that independence — keeping pre-marital assets in your own name, why prenups are actually one of the most honest conversations you can have with a spouse (you're agreeing on the rules while you still like each other), and why Emily and Jessica themselves handle their finances differently — and both approaches work. You'll also walk away with one concrete next step: how to have a "money date" with your spouse that's actually an honest conversation about where you are and where you're going — not just a bill-paying session. It's the kind of thing smart couples do, and it makes everything else easier. ☕ Today's sip: The Poppy blend from Yellow Coffee and Lost Sock Roasters — a bold espresso blend from local DC roasters. Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures 0:00 — What We're Sippin' On Today 0:24 — Financial Independence Within Marriage 3:15 — Breadwinner Mindset And Passport Metaphor  11:36 —  Joint Vs Separate Money Systems 14:21 — Values, Money History, Money Dates 18:58 — Transparency, Respect, And Closing   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

  2. APR 30

    The Stock Option Decision You Keep Putting Off

    You have stock options. You know they matter. And somewhere between the complexity, the tax implications, and a calendar full of more urgent things, they've landed in the "I'll deal with it later" pile. But here's the deal: later usually means a deadline is making the decision for you — and that's rarely optimal. In this episode, Emily and Jessica walk through what intentional stock option planning actually looks like in practice: why timing your exercise earlier often unlocks better outcomes, how the tax picture shifts dramatically depending on whether you have ISOs or NSOs, and how to think strategically about what you own after you exercise. They also surface the details that are easy to miss and expensive to ignore — the 90-day clock that starts ticking the moment you leave a company, the $100K ISO rule, and why your CPA needs a seat at this table before you make a move. If your options have been waiting for the "right time," this episode is 20 minutes well spent. ☕ Today's sip: Wright Tea Company's Sage Rose — a white tea with sage and rose from a Baltimore-based, women-owned company. Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   0:00 — When should I exercise my stock options? 2:12 — What We're Sippin' on Today  2:51 — Stock Options 101: The Basics and the Timeline  5:08 — NQSOs: What You'll Owe and How Cashless Exercise Works  7:50 — ISOs: The Holding Period and the AMT Risk  11:58 — Private Company Options: The Uncertainty and the Liquidity Problem  14:37 — The Case for Exercising Earlier Than You Think  18:18 — After You Exercise: Sell Immediately or Hold?  23:47 — The 100K ISO Rule and What Happens When You Leave  26:32 — Subscribe and Stay in Touch   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/

    29 min

  3. APR 15

    RSUs: What to Do When They Vest

    Your RSUs vest. The shares hit your account. Now what? For most high earners, RSUs sit in a kind of planning no-man's-land — not quite a paycheck, not quite an investment you picked, but treated like both without a clear strategy for either. The result is decisions made by default rather than intention. In this episode, Emily and Jessica walk through how RSUs actually work — from grant to vest to sale — and more importantly, what that means for your W-2, your tax bill, your concentration risk, and your broader financial picture. They get into when selling at vest makes sense, how to think about diversification when a significant portion of your wealth is tied to your employer's stock, and the details that are easy to miss and expensive to ignore — like the gap between your company's 24% withholding and your actual tax rate. If your RSUs have been a "figure it out later" item on your list, this one's worth the 20 minutes. ☕ Today's sip: Commonwealth Joe's Shenandoah Spring mix   0:00 The RSU Sell Or Hold Question 1:27 What We're Sipping On and the Listener Question  3:00 RSU Basics: Grant, Vest, Sale 7:22 Optionality And Concentration Risk 14:19 Tax Withholding Surprises And Planning 17:20 Wash Sale Rules With ESPP Shares 18:38 Takeaways    Please see important podcast disclosure information at 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. APR 1

    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

  5. 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

  6. 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

  7. 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

  8. 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
See All (20)

5
out of 5
7 Ratings

About

Time for a coffee break? Jessica Gibbs, CFP®️ and Emily Harper, CFP®️ answer the most pressing questions successful people ask about using their wealth to create an option-rich life—served one sip at a time. Have a question you want answered? Send it to: betweensips@monumentwm.com

Information

  • Creator
    Monument Wealth Management
  • Years Active
    2025 - 2026
  • Episodes
    20
  • Rating
    Clean
  • Copyright
    © Monument Capital Management
  • Show Website
    Between Sips