Between Sips

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

How to Split Assets Fairly Among Kids 08/05/2026

How to Split Assets Fairly Among Kids When children are young, dividing everything equally makes complete sense. But as your family evolves, adult children forge different paths. Some launch successful careers in high-tax states, while others step into caregiving roles, run family businesses, or need long-term support. Defaulting to an even split might seem like the easiest way to avoid conflict, but it often overlooks what is genuinely fair. In this episode, Emily and Jessica explore how to approach estate planning with nuance. They break down the friction points that arise when lifetime financial support, varying income levels, and complex tax rules interact with standard estate documents. The conversation explores why pre-tax retirement money and appreciated brokerage accounts shouldn't be treated equally, and how to offset lifetime gifts like down payments without creating sibling friction. Whether your goal is to minimize your heirs' tax liability or find strategic ways to hand down physical real estate or business interests fairly, this episode is for you. ☕ Today's sip: Si Mi Amour Cuban Coffee Queen Roasters blend brought back from Key West, Florida by one of our listeners :) 0:00 - What We’re Sippin’ on Today 0:55 - Equal Is Simple But Not Always Fair 6:28 - Lifetime Gifts Change The Math 8:29 - Taxes Can Make Equal Unequal 12:51 - Step Up In Basis Explained 15:13 - How To Monitor Fairness Over Time 18:24 - Business Property And Special Needs 21:16 - Caregiving And Reimbursing A Child 23:33 - Transparency And A Letter Of Instruction 25:24 - Subscribe Newsletter And Closing 25:46 - Important Disclosures 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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/42315930

Am I Financially “Okay”? The Myth of the Magic Number 07/22/2026

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: Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/ Instagram: Listen to Off The Wall, our podcast with market analysis: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/42173490

Making the Leap to Self-Employment: Know Your Worth 07/08/2026

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: 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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/41997285

No Kids? Here's What Your Estate Plan Actually Needs 06/24/2026

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: 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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/41748880

Smarter Ways to Share Wealth With Your Kids 06/10/2026

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: 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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/41587300

The Invisible Balance Sheet of Successful Families 05/27/2026

Marriage + Money: What Women Need to Know 05/13/2026

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: 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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/41264840

The Stock Option Decision You Keep Putting Off 04/30/2026

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: 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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/41054275

RSUs: What to Do When They Vest 04/15/2026

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: /episode/index/show/89f9d146-97f8-4655-a003-d7bb3c3fa3b3/id/40702565