Between Sips

Monument Wealth Management
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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. ٢٢ يوليو

    Am I Financially "Okay"? The Myth of the Magic Number

    Have you ever caught yourself staring at your net worth statement wondering: Am I financially okay? Or, What's the number I need to feel stable? Here's the thing: being okay is a feeling, not a figure. And the idea of a single "magic number" is mostly a myth. In fact, a Nationwide survey found only 38% of investors even believe in having one.  For high earners, that feeling looks completely different from person to person. One person's number is $8M. Another is $30M. What separates them isn't math — it's upbringing, lifestyle, and clarity on the goals and opportunities that lie ahead of them. Fixating on a net worth target amount misses the things that actually move it: rising healthcare costs, inflation, market volatility, and then—the questions of optionality: Can you afford to pivot careers? Retire early? Take a sabbatical? Absorb an accident or disability without it derailing everything else? A number on a page doesn't answer any of that on its own. So if it's not a number, how do you know you're on track? Emily and Jessica walk through their framework including: cash flow-based planning, probability modeling, and adequately protecting yourself against life's uncertainties. The takeaway: there's no magic number — just a probability of success you're comfortable with, protections that actually hold up, and knowing where your money is going.    0:00 — What We're Sippin' on Today 0:54 — Defining What "Okay" Means 4:22 — The Universal Track Signals 9:09 — Protections For Life's Surprises 12:18 — The Myth Of A Magic Number 16:44 — Cash Flow Planning And Probabilities of Success 22:23 — Near Term Cash And Portfolio Risk 24:54 — Subscribe And Get Our Newsletter 25:26 — Final Disclosures Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   Connect with us:  Get our Newsletter: https://www.monumentwealthmanagement.com/subscribe  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/

  2. ٨ يوليو

    Making the Leap to Self-Employment: Know Your Worth

    You've built a great corporate career. You've climbed the ladder, hit your stride, and established real stability. But for high-achieving executives, the next logical evolution may not be another corporate promotion, but taking your expertise into independent consulting, a business ownership portfolio, or an equity partnership. When successful, high-achieving professionals make the leap from a traditional W-2 role into entrepreneurship, it's easy to focus entirely on the opportunity ahead and miss the underlying compensation shifts. Moving between these two compensation systems introduces a unique set of cash flow considerations that should be actively managed to maintain momentum. In this episode, Emily and Jessica walk through what leaving traditional employment actually means for your money—and how to stay in the driver's seat. Because an executive-level move is about more than simply replacing your base salary; it's knowing the value of your total compensation. They look under the hood at how to strategically value every piece of the shift to self-employment—from capturing mid-year bonus cycles and accelerating unvested equity timelines to replacing benefits like insurance plans or 401k contributions you receive beyond your salary. They also cover the structural tax and benefit realities that are easy to miss and expensive to fix—including the out of pocket cost of self-employment taxes, retirement planning, and why you want to explore insurance coverage before you give your notice. If you've been looking at self-employment as just your next exciting career chapter, this episode gives you the insight to support your strategy. ☕ Today's sip: English Garden Herbal Tea Blend from Starbright Farm, a family-owned lavender farm in Whitehall, Maryland.   0:00 - What We're Sippin' on Today 6:02 - How to Calculate Your Total Compensation 8:03 - Self-Employment Taxes And Quarterly Payments 11:34 - Separate Accounts To Stabilize Cash Flow 12:48 - Negotiating Your Exit  13:55 - Health Insurance Costs And COBRA Timing 18:49 - Retirement Match Vesting, PTO And FSAs 20:51 - Noncompetes And Separation Agreement 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/# Listen to Off The Wall, our podcast with market analysis: https://monumentwealthmanagement.com/off-the-wall-podcast/

  3. ٢٤ يونيو

    No Kids? Here's What Your Estate Plan Actually Needs

    You've built substantial wealth through a high-earning career or business enterprise, carefully navigating your path with dedication. But when you sit down to formalize an estate plan, you quickly run into a frustrating reality: almost every estate planning blueprint assumes a linear default of passing everything down to your children. When you don't have children, the standard playbook completely breaks down. Without a default path, you have to be far more intentional about creating a highly customized framework that outlines who will step into critical decision-making roles during your lifetime and where your hard-earned assets will ultimately go. In this episode, Emily and Jessica break down why over 70% of child-free adults have zero formal legal planning in place and how to overcome the decision paralysis that holds many back. They look past standard templates to discuss how to separate personal trust from operational suitability when choosing executors and powers of attorney, so your autonomy is protected as you age. They also cover structural alternatives to traditional wealth transfers, the tactical advantages of active gifting while you are alive, and how to build custom trust structures to look after aging parents without losing control over the ultimate destination of your remaining wealth. If you want to move away from cookie-cutter legal templates and learn how a qualified estate attorney can build a sophisticated framework for your child-free estate, this conversation is for you. ☕ Today's sip: ONDA Coffee Roasters from Seattle, Washington, featuring an innovative revenue-share model that connects coffee drinkers directly with the growers who cultivate the beans. 0:00 — What We're Sippin' on Today 0:03 — The Big Question For Child-Free Plans 3:56 — Choosing Executors And Powers Of Attorney 7:55 — Long-Term Care Costs And Elder Risk 14:06 — Legacy Choices: Family, Friends, Charity 21:23 — Parents Trust Structures And Hiring A Lawyer 22:24 — Wrap-Up Subscriptions And Newsletter 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/

  4. ١٠ يونيو

    Smarter Ways to Share Wealth With Your Kids

    You've spent decades building your wealth, navigating market cycles, and making intentional sacrifices to secure your financial foundation. But a new question arises: At what point does it make sense to start sharing that success with your adult children? Waiting until your children are in their 60s or 70s to inherit wealth often misses the window where that money possesses the highest utility. Today's young adults are navigating a fundamentally compressed economic landscape, facing staggering starter-home prices, several-thousand-dollar childcare line items, and rising healthcare premiums. They are often in their peak expense years long before they hit their peak earning years. In this episode, Emily and Jessica break down why gifting assets while you are alive can be a far more powerful strategy for your family's trajectory. They demystify the gifting rules and limits, and outline strategic alternatives to gifting cash that can help ease your children's financial fatigue without spoiling their work ethic. They also cover strategies like paying tuition or medical bills directly to providers, funding 529 plans for grandchildren, and jumpstarting a child's retirement through targeted IRA contributions.  If you want to experience one of the joys of your success by seeing your wealth put to work when your family needs it most, this conversation is for you. ☕ Today's sip: Mexican Roast from Traeger Brothers, a roaster outside of Charlottesville, Virginia, featuring big citrus, tangerine, and orange notes fused with milk chocolate. 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/

  5. ٢٧ مايو

    The Invisible Balance Sheet of Successful Families

    Most wealth transfers fail by the third generation. It's a staggering statistic, but the reason behind it is rarely a bad investment strategy or a poorly drafted legal document. In this episode, Emily and Jessica explore why a solid estate plan is only one piece of the legacy puzzle. They break down the Five Forms of Capital: Human, Intellectual, Social, Spiritual, and Financial and explain why the four invisible forms are the ones that actually determine if your wealth will sustain your family or erode it. They discuss how to move past the logistics of tax minimization and asset titling to focus on what really matters.  If you want to learn about transferring values, building a shared purpose, and teaching the next generation how to be good stewards of their inheritance, this episode is for you. ☕ Today's sip: Yamamotoyama's  Ginger Yuzu Green Tea. A bold, family-owned brew from a company that has mastered the art of legacy since 1690. Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures   0:00 — What We're Sippin' on Today 0:23 — Tea Talk And The Legacy Gap 2:40 — The Five Forms Of Family Capital 11:54 — What Successful Families Do Differently 13:57 — Why Social Capital Is So Hard 15:17 — Keep Legacy Conversations Simple 18:04 — Easy First Steps To Start Today   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/

  6. ١٣ مايو

    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/

  7. ٣٠ أبريل

    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/

  8. ١٥ أبريل

    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/

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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

المعلومات

  • صناع العمل
    Monument Wealth Management
  • سنوات النشاط
    ٢٠٢٥ - ٢٠٢٦
  • الحلقات
    ٢٥
  • التقييم
    ملائم
  • حقوق النشر
    © Monument Capital Management
  • موقع البرنامج على الويب
    Between Sips